Operations Training Specialist, Claims

About the role

The Operations Training Specialist on our Enablement team will own the full training lifecycle for Sidecar Health's operations teams. This is a hands-on role where you design the content, facilitate sessions, manage logistics, and ensure outcomes from new hires' first days through independent performance.

Responsibilities

• Own the end-to-end new hire onboarding experience for assigned operations teams — program design, content creation, classroom delivery, nesting coordination, job shadowing, and floor readiness evaluation.
• Design and facilitate ongoing refresher, upskilling, and process change training as business needs evolve — including queue-specific training across Claims adjudication workflows.
• Build and maintain all training materials for assigned teams — e-learning modules, Adobe Captivate simulations, facilitator guides, presentations, knowledge checks, role-play scenarios, and assessments.
• Contribute to building a repeatable Claims training library — queue-specific modules that can be deployed consistently over time, reducing dependency on tribal knowledge or one-off preparation.
• Own operations-specific knowledge content within the knowledge management system, ensuring accuracy and alignment with current policies, workflows, and product changes.
• Assess the training and knowledge impact of operational and product changes as they come through, and proactively develop or update materials to support those changes.
• Scope and execute lighter knowledge and training updates independently, escalating larger program changes to the broader Enablement team for design input.
• Manage all program logistics independently: LMS administration, scheduling, roster management, Zoom coordination, and SME preparation and briefing.
• Collaborate with the broader Enablement team on knowledge management, L&D initiatives, and operational content projects.
• Use AI-assisted tools to develop content efficiently, with full accountability for review and quality of all outputs.

Requirements

• 3+ years of experience in training, instructional design, or knowledge management, ideally within a contact center, healthcare operations, or customer service environment.
• Bachelor's degree or equivalent relevant experience in a similar role.
• Demonstrated end-to-end ownership of training programs — you have built them, run them, and improved them without requiring step-by-step direction.
• Strong project and time management skills, with the ability to manage multiple workstreams and deadlines concurrently.
• Clear and proactive communication skills, with experience delivering training sessions virtually and in person.
• Familiarity with knowledge management systems, learning management systems (LMS), or other documentation tools.
• Collaborative mindset, with the ability to partner across teams and departments.
• A proactive, ownership-driven approach to managing training programs and knowledge resources.
• Knowledge of instructional design principles and adult learning methodologies.
• Comfort with AI-assisted content development tools and strong editorial judgment about quality and accuracy of outputs.

Preferred, Not Required

• Experience in healthcare claims processing, claims adjudication, or health insurance operations.
• Experience designing or facilitating training in a claims or healthcare operations environment.
• Familiarity with simulation-based training tools such as Adobe Captivate.
• Prior experience with Sana, Document360, or similar LMS and knowledge management platforms.

Benefits

Competitive salary ($68,000 - $75,000), bonus opportunity, and equity package. 401(k) retirement plan with company match. Paid vacation and company holidays. Opportunity to make a direct impact on member experience and employee success. Opportunity to make a meaningful impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.

Schedule

Full-time position.

Pay

$68,000 - $75,000 annually.